Ethylenediaminetetraacetic Acid → 4-Methoxy-2-methylpyridine

HRID 273326

反応式

HRID 273326 の反応式
[Cl-].C[Zn+].Cl[C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][N:6]=1.[CH2:13](N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.C([O-])([O-])=O.[K+].[K+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([CH3:13])[CH:10]=1

参加物

7

反応物 4

HCID 6049Ethylenediaminetetraacetic AcidHCID 11430Potassium CarbonateHCID 19911282-Chloro-4-methoxypyridineHCID 178477797HCID 178477797、化合物

生成物 1

HCID 47377584-Methoxy-2-methylpyridine収率 50%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Methylzinc chloride in THF (2 M, 10.489 mL, 21 mmol) was added to a solution of 2-chloro-4-methoxypyridine (0.500 g, 3.48 mmol) and Pd(PPh3)4 (0.161 g, 0.14 mmol) in THF (10 mL). The mixture was refluxed for 40 h and then poured into an aqueous solution (10 mL) containing ethylenediaminetetraacetic acid (1.5 g). The resulting mixture was neutralized with K2CO3 and extracted with Et2O. The organic layer was concentrated to give a residue, which was purified on a silica gel column eluting with MeOH:EtOAc (1:10) to give 4-methoxy-2-methylpyridine (0.213 g, 50.0%).

後処理

  1. temperatureThe mixture was refluxed for 40 h
  2. extractionextracted with Et2O
  3. concentrationThe organic layer was concentrated
  4. customto give a residue, which
  5. customwas purified on a silica gel column
  6. washeluting with MeOH:EtOAc (1:10)

出典と根拠

ORDレコード
ord-e810fdf5a0ca4f1d9c55403b4f5a9099
出典データセット
uspto-grants-2008_11
特許番号
US07456289B2

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